p-Chlorothiophenol → (4-Chlorophenyl)(2,5-difluorobenzyl)sulfane

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[Na+].[F:11][C:12]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:13]=1[CH2:14]Br>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:14][C:13]2[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:12]=2[F:11])=[CH:4][CH:3]=1

Participants

Procedure

4-Chlorothiophenol (253 g, 1.75 mol) was dissolved in industrial methylated spirits (1265 mL) and 2M sodium hydroxide solution (901 mL) was added, maintaining the temperature below 20° C. A solution of 2,5-difluorobenzyl bromide (355 g, 1.72 mol) in industrial methylated spirits (250 mL) was added dropwise to the thiolate solution, maintaining the temperature below 15° C. Upon completion of the reaction, water (1000 mL) was added. The resulting slurry was aged at 5° C. and then filtered. The cake was washed sequentially with cold industrial methylated spirits:water (40:60) and then water (500 mL). Drying in vacuo at ambient temperature furnished 2-[[(4-chlorophenyl)thio]methyl]-1,4-difluorobenzene (462.3 g, 99.6%). 1H NMR (CDCl3)—as obtained for the corresponding intermediate of Method (a).